Free I'm Dying Up Here: Heartbreak and High Times in Stand-Up Comedy's Golden Era by William Knoedelseder by William Knoedelseder Page B

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    William Knoedelseder
    Letterman learned one day when George suckered him into shooting free throws for money. Letterman was stunned to find himself suddenly down $100 that he could not afford.
    “I don’t understand,” George said. “If you were so concerned about losing the money, then why did you bet? ”
    Letterman looked at his doughy friend and replied, “Because it never occurred to me that I would lose to you. ”
    Letterman found Miller’s myriad idiosyncrasies endlessly amus-ing. But what he liked most about George was his wry wit and superb joke-writing skills. Miller was a master of the one-line setup and quick punch line, a kind of joke haiku that always cut to the core but was never mean-spirited. He was an irascible character but still sweet natured. “George goes for the jugular,” Elayne Boosler liked to say, “but never with his teeth, only with his gums. He’ll gum you to death.”
    For his part in the friendship, Miller seemed to like nothing more than to tweak Dave’s natural state of unease. One evening he was having sex with a girlfriend on his couch when Letterman walked into the apartment without knocking. Letterman was hor-ribly embarrassed, which Miller thought was a hoot. From then on, he made a point of always making love to the girl on the couch with the door unlocked in the hope that Letterman would walk in on them again. He got Dave one more time, but after that Dave always knocked.
    Letterman would downplay his relationship with Leno in later years, but he was drawn strongly to Jay in the early days. The initial attraction was professional rather than personal. He admired, even envied, Leno’s onstage craft. Letterman was never comfortable in the nightclub arena, always thought his performances were subpar, and constantly felt like an imposter in the company of real comics like Leno, Miller, and Dreesen. Leno, on the other hand, had confidence to burn and never seemed to sweat a blown line or a bad audience. Everything rolled off his back.
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    Letterman loved Leno’s attitude and marveled at his ability to sell even a mediocre joke to a crowd. “Jay is absolutely the best at observational stuff,” he told the Los Angeles Times in one of his earliest press interviews. “He has an amazing ability to take everyday stuff to the stage and make it work nine times out of ten.”
    Letterman observed about Leno’s act that he won over the audience by treating them as if they were a group of his hip friends.
    They were all in it together, laughing at the absurdities of the world.
    Leno was equally impressed with Letterman. He noted that Letterman was not one to work the room or prowl the stage, but he was a superb wordsmith who radiated smarts and constantly came up with some of the most original material he’d ever heard.
    They quickly formed a mutual admiration society, watching and learning from one another. Night after night at the Comedy Store, when they weren’t onstage, they were standing together in the back, taking it all in, studying everything. Their fellow comics came to think of them almost as a team, connected by an amper-sand like Abbott & Costello or Martin & Lewis. The consensus in the comedy community was that Leno & Letterman (or vice versa) were destined for big things.
    Proving Tom Dreesen’s dictum about comics getting each other work, Letterman landed his first paying job in Los Angeles working with Leno as a joke writer for Jimmie Walker. They were each paid $100 a week and expected to come up with fifteen acceptable jokes. Their employer was actually Walker’s company, shamelessly named Ebony Genius Management, which was run by Walker’s managers, Helen Gorman and Jerry Kushnick, who eventually married. They quickly signed Leno and Letterman to talent contracts but saw Letterman primarily as a writer, not a